Stereoselective hydrogenation of (−)-menthone and (+)-isomenthone mixture using nickel catalysts

Stereoselective hydrogenation of (−)-menthone and (+)-isomenthone mixture using nickel catalysts
Kukula, Pavel; Červený, Libor
2000-01-01 00:00:00
The catalytic hydrogenation of an optically active mixture of (−)-menthone and (+)-isomenthone was studied. The catalysts Raney nickel and Ni/SiO2 were used for these hydrogenations. Catalysts modified with (2R,3R)-(+)-tartaric acid were tested as well. Various non-equilibrium mixtures of isomers were produced by means of these reactions, especially mixtures containing the less stable menthol isomers, (+)-neomenthol and (+)-neoisomenthol. (−)-Menthol was produced during these reactions to a limited extent, the production of (−)-isomenthol was barcly existent. Isomerization of (−)-menthone and (+)-isomenthone occurred during these reactions. Isomerizations among individual isomers were barely detectable. The catalysts used showed a very low activity under the given reaction conditions.
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Stereoselective hydrogenation of (−)-menthone and (+)-isomenthone mixture using nickel catalysts